The proposed research consists of the first nonracemic synthesis of Roseophilin. Roseophilin has been shown to have potent cytotoxic properties against K562 human erythroid leukemia and KB human epidermoid cells. The proposed total synthesis will involve a chiral tetrazine Diels-Alder reaction, McMurry reductive carbonyl coupling, and acyl radical-alkene ring closing as the key steps. Based on structural relationships to a family of similar cytotoxic compounds, a linker will be attached in an effort to identify Roseophilin's biological target.